US4441884A - Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers - Google Patents

Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers Download PDF

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Publication number
US4441884A
US4441884A US05/959,211 US95921178A US4441884A US 4441884 A US4441884 A US 4441884A US 95921178 A US95921178 A US 95921178A US 4441884 A US4441884 A US 4441884A
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US
United States
Prior art keywords
process according
formula
phenyl
compound
naphthyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US05/959,211
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English (en)
Inventor
Hans-Peter Baumann
Urs Mosimann
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Fidelity Union Bank
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Sandoz AG
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Assigned to SANDOZ LTD. (A/K/A SANDOZ AG) reassignment SANDOZ LTD. (A/K/A SANDOZ AG) ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: BAUMANN, HANS-PETER, MOSIMANN, URS
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Publication of US4441884A publication Critical patent/US4441884A/en
Assigned to FIDELITY UNION TRUST COMPANY reassignment FIDELITY UNION TRUST COMPANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: SANDOZ LTD. (A/K/A SANDOZ AG)
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
    • C09B62/24—Azo dyes
    • C09B62/245—Monoazo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/655—Compounds containing ammonium groups
    • D06P1/66—Compounds containing ammonium groups containing quaternary ammonium groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention relates to a treatment process for polyamide fibres.
  • the present invention provides a process for treating a polyamide textile substrate to increase the affinity thereof for anionic dyes or to reserve same against cationic dyes, comprising applying thereto, in a weakly alkaline medium, a compound of formula I, ##STR2## wherein
  • R is phenyl; naphthyl; (C 5-6 )cycloalkyl; or phenyl or naphthyl substituted by a total of up to 3 substituents selected from the group consisting of (C 1-4 )alkyl, chlorine and bromine (maximum of two of each of these);
  • each of R 1 and R 2 independently, is (C 1-4 )alkyl, and X.sup. ⁇ is a non-chromophoric anion.
  • R is preferably phenyl, tolyl, xylyl, naphthyl, naphthyl monosubstituted by methyl or chlorine, cyclopentyl or cyclohexyl, more preferably phenyl, naphthyl or cyclohexyl with phenyl being especially preferred.
  • each of R 1 and R 2 is methyl or ethyl, more preferably both of R 1 and R 2 are methyl.
  • X.sup. ⁇ is preferably Cl.sup. ⁇ , Br.sup. ⁇ , I.sup. ⁇ or CH 3 SO 4 .sup. ⁇ , more preferably Cl.sup. ⁇ or Br.sup. ⁇ .
  • the compounds of formula I also form part of the present invention.
  • Preferred compounds of formula I are those in which R is phenyl, naphthyl or cyclohexyl, R 1 and R 2 are both methyl and X.sup. ⁇ is a non-chromophoric anion, preferably Cl.sup. ⁇ , Br.sup. ⁇ , I.sup. ⁇ or CH 3 SO 4 .sup. ⁇ , more preferably Cl.sup. ⁇ or Br.sup. ⁇ .
  • the compounds of formula I may be prepared in accordance with known methods from available starting materials, for example by methods analogous to those described in U.S. Pat. Nos. 2,876,217 and 2,995,513.
  • the compounds of formula I may be applied to the polyamide substrate by known methods, for example by printing with pastes containing a compound of formula I, spraying or sprinkling the fibres with solutions containing a compound of formula I, or by treating the substrate in a bath containing a compound of formula I in solution, e.g. by the exhaust method.
  • the amount of compound of formula I in the pastes or solutions is preferably in the range of from 0.1% to 5%, by weight based on total weight of paste or solution, more preferably from 0.2% to 5%, even more preferably from 0.2% to 4%, with from 0.5% to 4% being especially preferred.
  • the process of the present invention is carried out in a weakly alkaline medium i.e. a medium having a pH value of from 7 to 10, preferably in a medium having a pH value in the range of from 7.2 to 9.
  • the weakly alkaline medium is preferably obtained by adding a weakly alkaline salt such as for example sodium bicarbonate, preferably in an amount of from 0.1 to 2%, more preferably from 0.5 to 2%, by weight, based on the total weight of the paste or solution.
  • the paste or solution may also contain sodium sulphate in addition to the weakly alkaline salt.
  • the pastes or solutions contain from up to 10%, more preferably from 0.5 to 10%, most preferably 1 to 5% by weight based on the weight of the paste or solution of such sodium sulphate.
  • Fixation may be accomplished by any of the known methods, for example by treating the substrate in saturated steam for a period of from 2 to 10 minutes, treating it with hot air for about 1 minute, or storing the substrate at room temperature for one or two days.
  • the compounds of formula I may be made up into pastes and solutions in accordance with known methods, for example pastes by mixing with the usual additives such as stabilizers, thickeners etc.
  • the substrate to be treated may be of natural or synthetic polyamide, for example wool, silk, Nylon 6, Nylon 66 and Nylon 11 and may be in fibre, fabric or yarn form.
  • the polyamide may, of course, be in blend form, such blend preferably containing at least 50% by weight of polyamides.
  • the preferred process according to the invention comprises applying a paste containing a compound of formula I by a printing process, followed by fixation.
  • anionic dye is to be understood to include anionic optical brighteners as well as dyestuffs.
  • the two types of dyes are of different colour, which possibilities can be further enhanced by applying a reserving agent to anionic dyes in local areas.
  • the treatment of the substrate with the compounds of formula I has no effect on the affinity of the substrate for disperse dyes and accordingly still further effects, as desired, can be achieved by additional dyeing with a disperse dye or dyes, e.g. to give a ground colour.
  • dyeings made with anionic dyes on polyamide fibres treated in accordance with the process of the present invention possess improved wet-fastness.
  • polyamides treated in accordance with the present invention may be dyed or printed in accordance with known methods, for example by exhaust dyeing, pad dyeing or one of the many printing techniques.
  • both pastes being made up to a total of 1000 parts with water.
  • dyestuffs (a), (b) and (c) are carried out in the presence of 2% acetic acid and with dyestuff (d) in the presence of 4% ammonium sulphate.
  • the material dyed with dyestuff (a) is red, with dyestuff (b) blue, with dyestuff (c) greenish-blue and with dyestuff (d) yellowish-red. It is observed that the pre-printed strips are dyed to a greater depth of shade than the un-printed strips.
  • the strips pre-treated with 30 parts of the compound of formula III are of a significantly greater depth of shade than those pre-treated with 5 parts of the compound of formula III.
  • the pastes are homogenised by vigorous stirring.
  • Acid Yellow 19 Acid Yellow 25, Acid Yellow 127, Acid Orange 3, Acid Orange 19, Acid Orange 43, Acid Red 57, Acid Red 145, Acid Red 151, Acid Blue 23, Acid Blue 25, Acid Blue 40, Acid Blue 52, Acid Blue 80, Acid Blue 92, Acid Blue 268.
  • the treated portions are dyed with a greater depth of shade than the untreated portions.
  • the patterns are clearly visible.
  • the printed patterns are maintained even after several hours dyeing at boiling temperature.
  • Example 2 The procedure described in Example 2 is repeated using the described pastes and also a further one of the following composition:
  • Dyeing with an anionic dyestuff the portions of the fabric treated with the compounds of formula II and III are significantly more deeply dyed, and the portions treated with 2,4-dichloro-6-phenylamino-1,3,5-triazine-4'-sulphonic acid are significantly more weakly dyed than the untreated portions.
  • cationic dyestuffs When cationic dyestuffs are used, the picture is reversed. (With disperse dyestuffs no effect is shown with this treatment). A large variety of shades and depth of shades can be obtained when such pre-treated material is dyed. For example:
  • Texturised Nylon 66 and Nylon 6 carpet yarn are printed with a paste of the following composition by the warp printing method (take-up of 100% on the printed portions)
  • composition as for 1st printing roll except that 3.75 parts of the compound of formula III are used.
  • the printing by the second printing roll crosses that of the first printing roll.
  • the printed material is steamed in saturated steam at 102°-103° for 4 minutes and then rinsed with water.
  • the yarn treated as described above is tufted on jute fabric, and samples of the resulting carpet are dyed by the exhaust method.
  • Acid Yellow 25 Acid Red 57 and Acid Blue 72 dyestuffs, the following shades are obtained: beige, grey, red, blue and olive. All the carpet samples display the so-called "space dyed effect".
  • Example 4 The procedure of Example 4 is repeated but replacing the paste of the 2nd printing roll with the following composition:
  • the treated material is steamed in saturated steam at 102°-103° for 7 minutes and then rinsed with water. After subsequent dyeing the following four levels of affinity are to be seen:
  • Combed wool is printed by the Vigoureux method with pastes of the following composition:
  • the weight increase on the printed portions is 100%.
  • the combed wool After the combed wool has been steamed in saturated steam at 102°, rinsed and dried, it is converted into yarn.
  • the yarn is dyed conventionally by the exhaust method, dyed fabres of various depths are observed. For example, when 1% of the dyestuff of formula ##STR5## together with 1% of alkoxylated and sulphated N-aminopropyl tallow fatty acid amine is used, light and dark red fibres are observed.
  • Nylon-6, -66 and -11, wool and silk in the form of flocks or yarn are treated in each case with 1 part of the compound of formula II or III dissolved in 1000 parts of water.
  • the cold treatment bath is heated to boiling point over a period of 30 minutes and the treatment at boiling point is continued for a further 30 minutes.
  • the material sample is then removed from the bath, rinsed with water and dried, whereafter it is processed together with the corresponding untreated material to yarn or twisted yarn.
  • each material sample After dyeing with an anionic dyestuff each material sample displays darker and lighter parts, the former being attributed to the pre-dyeing treatment.
  • Nylon-6 and Nylon-66 pullovers are in each case irregularly sprayed with 1% solutions of the compounds of formulae II and III, which solutions further contain 1% of sodium bicarbonate.
  • the pullovers are stored for a day at room temperature and then rinsed with water, whereafter they are dyed by the exhaust dyeing method with Acid Blue 92, Acid Red 145 and Direct Green 28.
  • Nylon-66 satin is printed by the screen printing process with a paste of the following composition: (100% increase in weight of treated portions)
  • the paste is intensively rubbed to achieve homogeneity.
  • the printed material is dried, fixed in a hot air current at 160° for 60 seconds and then rinsed.
  • Pieces of the material are than dyed with various combinations of anionic dyestuffs.
  • the printing pattern is observed to be very clear in that the treated portions are significantly more deeply dyed than the untreated portions.
  • the compound of formula II may be prepared mixing 448 g N-benzyldimethylamine in 118 g water and neutralizing the same with 369.5 g hydrochloric acid. 304.8 g epichlorohydrin are added dropwise thereto at 50° C. After the exothermic reaction is complete the reaction mixture is heated to 90° C. and stirred at this temperature for 45 minutes, the water is distilled off and the product which is a white powder is dried.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US05/959,211 1976-12-07 1978-11-09 Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers Expired - Lifetime US4441884A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1535576A CH631589B (de) 1976-12-07 1976-12-07 Verfahren zur erhoehung der affinitaet fuer anionische farbstoffe und optische aufheller von textilmaterial.
CH15355/76 1976-12-07

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US05856395 Continuation-In-Part 1977-12-01

Publications (1)

Publication Number Publication Date
US4441884A true US4441884A (en) 1984-04-10

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Family Applications (1)

Application Number Title Priority Date Filing Date
US05/959,211 Expired - Lifetime US4441884A (en) 1976-12-07 1978-11-09 Quaternary ammonium compounds and their use as dyeing assistants for polyamide fibers

Country Status (10)

Country Link
US (1) US4441884A (enrdf_load_stackoverflow)
JP (1) JPS5374187A (enrdf_load_stackoverflow)
BE (1) BE861515A (enrdf_load_stackoverflow)
CH (1) CH631589B (enrdf_load_stackoverflow)
DE (1) DE2752660A1 (enrdf_load_stackoverflow)
FR (1) FR2373634A1 (enrdf_load_stackoverflow)
GB (1) GB1591857A (enrdf_load_stackoverflow)
HK (1) HK5082A (enrdf_load_stackoverflow)
IT (1) IT1090551B (enrdf_load_stackoverflow)
NL (1) NL7713367A (enrdf_load_stackoverflow)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4615709A (en) * 1983-12-16 1986-10-07 Ipposha Oil Industries Co., Ltd. Cationic compound, process for preparing same and treatment of textile material for improved dyeing
US4702742A (en) * 1984-12-10 1987-10-27 Canon Kabushiki Kaisha Aqueous jet-ink printing on textile fabric pre-treated with polymeric acceptor
US4838896A (en) * 1987-02-26 1989-06-13 Sandoz Ltd. Composition useful for aftertreating dyeings, printings and optical brightenings: epihaldhydrin-ammonia reaction product and allylamine polymer
US5698476A (en) * 1995-03-01 1997-12-16 The Clorox Company Laundry article for preventing dye carry-over and indicator therefor
US5830240A (en) * 1996-10-23 1998-11-03 Solutia Inc. Fibers and textile materials having enhanced dyeability and finish compositions used thereon
US5944852A (en) * 1996-10-23 1999-08-31 Solutia Inc. Dyeing process
US5948153A (en) * 1998-04-24 1999-09-07 Milliken & Company Water-soluble complexes of optical brighteners and quaternary ammonium compounds which are substantially free from unwanted salts
US6377478B1 (en) * 1999-05-28 2002-04-23 Toshiba International Corporation Inverter device
US20040121675A1 (en) * 2002-12-23 2004-06-24 Kimberly-Clark Worklwide, Inc. Treatment of substrates for improving ink adhesion to the substrates
US20060246263A1 (en) * 2005-04-29 2006-11-02 Kimberly-Clark Worldwide, Inc. Treatment of substrates for improving ink adhesion to the substrates
CN102978952A (zh) * 2012-12-21 2013-03-20 南通斯恩特纺织科技有限公司 活性染料生态低盐染色整理剂及其制备方法和应用

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2470185A1 (fr) * 1979-11-20 1981-05-29 Protex Manuf Prod Chimiq Application nouvelle des composes epoxyalkylammonium quaternaire au pretraitement des fibres de polyamide
US4380453A (en) 1980-02-06 1983-04-19 Dixie Yarns, Inc. Extraneous dye or colorant scavenging system in laundry
US4374639A (en) 1980-04-03 1983-02-22 Dixie Yarns, Inc. System for preventing static electricity on laundered textile materials
DE3151594A1 (de) * 1981-01-10 1982-08-26 Sandoz-Patent-GmbH, 7850 Lörrach Verfahren zur verbesserung faerberischer eigenschaften von polyamidfaser-textilmaterialien
CH660940GA3 (enrdf_load_stackoverflow) * 1981-01-10 1987-06-30
JPS60126389A (ja) * 1983-12-09 1985-07-05 ユニチカ株式会社 獣毛繊維の染色方法
JP5639348B2 (ja) * 2009-06-18 2014-12-10 旭化成せんい株式会社 ポリアミド繊維とポリウレタン繊維との混用糸条又は布帛の染色品
JP5639347B2 (ja) * 2009-06-18 2014-12-10 旭化成せんい株式会社 ポリアミド繊維とセルロース繊維とポリウレタン繊維との混用糸状又は布帛染色品

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2876217A (en) * 1956-12-31 1959-03-03 Corn Products Co Starch ethers containing nitrogen and process for making the same
US2995513A (en) * 1957-12-31 1961-08-08 Corn Products Co Flocculation by starch ethers
NL7006834A (enrdf_load_stackoverflow) * 1969-05-12 1970-11-16
US3652201A (en) * 1968-04-30 1972-03-28 Ciba Geigy Ag Process for the production of dyeings on fiber material consisting of polymeric or copolymeric acrylonitrile
US3685953A (en) * 1968-08-30 1972-08-22 Inst Textile De France Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles
DE2117182A1 (en) * 1971-04-08 1972-10-12 Bergmann, Gerhard, 5165 Niederau Increasing anionic dye receptivity of polyamide fibres - - by treating with amine-conggtg epoxy cpds, and heat-treatment
US3737406A (en) * 1971-03-22 1973-06-05 Alelio G D Reactive epoxy-onium catalysts for synthesis of polyoxazolidones
GB1352205A (en) * 1970-11-13 1974-05-08 Hoffmann Staerkefabriken Ag Process for the preparation of glycidyltrialkylammonium halides
US3853460A (en) * 1972-01-26 1974-12-10 Manuf De Prod Chem Protex Concentrated and stable salt compositions of epoxypropylammonium salts
US3988111A (en) * 1974-03-18 1976-10-26 Manufacture De Produits Chimiques Protex Process for the dyeing of textile fibers in an organic-system medium
US4035145A (en) * 1974-02-15 1977-07-12 Bayer Aktiengesellschaft Quaternary N-(2,3-epoxyalkyl)-ammonium compounds
US4090845A (en) * 1975-12-15 1978-05-23 Henkel Kommanditgesellschaft Auf Aktien Process for the dyeing of polyacrylonitrile fibrous material
US4149849A (en) * 1976-11-24 1979-04-17 Bayer Aktiengesellschaft Process for printing and dyeing

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2876217A (en) * 1956-12-31 1959-03-03 Corn Products Co Starch ethers containing nitrogen and process for making the same
US2995513A (en) * 1957-12-31 1961-08-08 Corn Products Co Flocculation by starch ethers
US3652201A (en) * 1968-04-30 1972-03-28 Ciba Geigy Ag Process for the production of dyeings on fiber material consisting of polymeric or copolymeric acrylonitrile
US3685953A (en) * 1968-08-30 1972-08-22 Inst Textile De France Dry heat reaction of quaternized epoxides and quaternized chlorohydrins with hydroxylated textiles
NL7006834A (enrdf_load_stackoverflow) * 1969-05-12 1970-11-16
GB1352205A (en) * 1970-11-13 1974-05-08 Hoffmann Staerkefabriken Ag Process for the preparation of glycidyltrialkylammonium halides
US3737406A (en) * 1971-03-22 1973-06-05 Alelio G D Reactive epoxy-onium catalysts for synthesis of polyoxazolidones
DE2117182A1 (en) * 1971-04-08 1972-10-12 Bergmann, Gerhard, 5165 Niederau Increasing anionic dye receptivity of polyamide fibres - - by treating with amine-conggtg epoxy cpds, and heat-treatment
US3853460A (en) * 1972-01-26 1974-12-10 Manuf De Prod Chem Protex Concentrated and stable salt compositions of epoxypropylammonium salts
US4035145A (en) * 1974-02-15 1977-07-12 Bayer Aktiengesellschaft Quaternary N-(2,3-epoxyalkyl)-ammonium compounds
US3988111A (en) * 1974-03-18 1976-10-26 Manufacture De Produits Chimiques Protex Process for the dyeing of textile fibers in an organic-system medium
US4090845A (en) * 1975-12-15 1978-05-23 Henkel Kommanditgesellschaft Auf Aktien Process for the dyeing of polyacrylonitrile fibrous material
US4149849A (en) * 1976-11-24 1979-04-17 Bayer Aktiengesellschaft Process for printing and dyeing

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4615709A (en) * 1983-12-16 1986-10-07 Ipposha Oil Industries Co., Ltd. Cationic compound, process for preparing same and treatment of textile material for improved dyeing
US4702742A (en) * 1984-12-10 1987-10-27 Canon Kabushiki Kaisha Aqueous jet-ink printing on textile fabric pre-treated with polymeric acceptor
US4838896A (en) * 1987-02-26 1989-06-13 Sandoz Ltd. Composition useful for aftertreating dyeings, printings and optical brightenings: epihaldhydrin-ammonia reaction product and allylamine polymer
US5698476A (en) * 1995-03-01 1997-12-16 The Clorox Company Laundry article for preventing dye carry-over and indicator therefor
US5830240A (en) * 1996-10-23 1998-11-03 Solutia Inc. Fibers and textile materials having enhanced dyeability and finish compositions used thereon
US5944852A (en) * 1996-10-23 1999-08-31 Solutia Inc. Dyeing process
US5948153A (en) * 1998-04-24 1999-09-07 Milliken & Company Water-soluble complexes of optical brighteners and quaternary ammonium compounds which are substantially free from unwanted salts
US6377478B1 (en) * 1999-05-28 2002-04-23 Toshiba International Corporation Inverter device
US20040121675A1 (en) * 2002-12-23 2004-06-24 Kimberly-Clark Worklwide, Inc. Treatment of substrates for improving ink adhesion to the substrates
US20060246263A1 (en) * 2005-04-29 2006-11-02 Kimberly-Clark Worldwide, Inc. Treatment of substrates for improving ink adhesion to the substrates
US8236385B2 (en) 2005-04-29 2012-08-07 Kimberly Clark Corporation Treatment of substrates for improving ink adhesion to the substrates
CN102978952A (zh) * 2012-12-21 2013-03-20 南通斯恩特纺织科技有限公司 活性染料生态低盐染色整理剂及其制备方法和应用
CN102978952B (zh) * 2012-12-21 2015-05-27 南通斯恩特纺织科技有限公司 活性染料生态低盐染色整理剂及其制备方法和应用

Also Published As

Publication number Publication date
FR2373634A1 (fr) 1978-07-07
GB1591857A (en) 1981-06-24
DE2752660C2 (enrdf_load_stackoverflow) 1987-09-24
FR2373634B1 (enrdf_load_stackoverflow) 1983-07-29
JPS619437B2 (enrdf_load_stackoverflow) 1986-03-24
BE861515A (fr) 1978-06-05
DE2752660A1 (de) 1978-06-08
IT1090551B (it) 1985-06-26
CH631589GA3 (enrdf_load_stackoverflow) 1982-08-31
NL7713367A (nl) 1978-06-09
HK5082A (en) 1982-02-19
JPS5374187A (en) 1978-07-01
CH631589B (de)

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